Synthesis of the (1â6)-linked thiodisaccharide of galactofuranose: inhibitory activity against a ß-galactofuranosidase.
Bioorg Med Chem
; 21(11): 3327-33, 2013 Jun 01.
Article
em En
| MEDLINE
| ID: mdl-23602520
A new (1â6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,ß-D-galactofuranosid)uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-ß-D-galactofuranoside (2ß) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-ß-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target ß-D-Galf-S-(1â6)-ß-d-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the ß-galactofuranosidase from Penicillum fellutanum (K(i)=3.62 mM).
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Penicillium
/
Tiogalactosídeos
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Proteínas Fúngicas
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Dissacarídeos
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Galactose
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Glicosídeo Hidrolases
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Antifúngicos
Idioma:
En
Revista:
Bioorg Med Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
Argentina
País de publicação:
Reino Unido